Thionyl Chloride → 2,2-DI(Acetoxymethyl)propionyl chloride

HRID 34519Notes

Reaction equation

S(Cl)([Cl:3])=O.[C:5]([O:8][CH2:9][C:10]([CH2:15][O:16][C:17](=[O:19])[CH3:18])([CH3:14])[C:11](O)=[O:12])(=[O:7])[CH3:6]>>[C:5]([O:8][CH2:9][C:10]([CH2:15][O:16][C:17](=[O:19])[CH3:18])([CH3:14])[C:11]([Cl:3])=[O:12])(=[O:7])[CH3:6]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 224578422,2-Bis(acetoxymethyl)propionic acid

Product 1

HCID 198190112,2-DI(Acetoxymethyl)propionyl chloride

Conditions

Temperature: 100 °C

Procedure

182 ml (2.5 moles) of thionyl chloride are poured over 218 g (1 mole) of 2,2-bis-acetonxymethyl propionic acid (step 1), followed by refluxing for 8 hours at a batch temperature of approximately 100° C. Excess thionyl chloride is distilled off in a water jet vacuum, leaving a pale yellow, oily product. Yield 236 g (100% of the theoretical).

Workup

distillationExcess thionyl chloride is distilled off in a water jet vacuum
customleaving a pale yellow, oily product

Sources & evidence

ORD record: ord-89530f2a18254553b1cad6d2f1223cf2
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04762777

Reaction notes

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